4-tert-Butylbenzoyl chloride → HCID 20085641, compound

HRID 1608821Notes

Reaction equation

HRID 1608821 reaction equation
[NH2:1][C:2]1[CH:17]=[CH:16][CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1)=[O:5].[C:18]([C:22]1[CH:30]=[CH:29][C:25]([C:26]([Cl:28])=[O:27])=[CH:24][CH:23]=1)([CH3:21])([CH3:20])[CH3:19]>>[ClH:28].[NH:13]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:8][CH2:7][NH:6][C:4](=[O:5])[C:3]1[CH:14]=[CH:15][CH:16]=[CH:17][C:2]=1[NH:1][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([C:18]([CH3:20])([CH3:19])[CH3:21])=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 743724-tert-Butylbenzoyl chlorideHCID 200855782-Amino-N-[2-(1H-imidazol-2-yl)ethyl]benzamide

Product 1

HCID 20085641HCID 20085641, compoundYield 64.2%

Procedure

The titled compound was prepared substantially in accordance with the method detailed in Example 11 using 18.4 g (0.0799 mol) of 2-amino-N-[2-(1H-imidazol-2-yl)-ethyl]benzamide, prepared as in Example 6A, and 32.07 g (0.1598 mol) of p-tert-butylbenzoyl chloride, with the exception that after removing methanol the resultant oil was crystallized from ethyl acetate to provide an oily solid. This solid was purified by filtration through silica gel using 7% methanol in dichloromethane. The filtrate was reduced to dryness under reduced pressure and the resultant residue was recrystallized from an ethyl acetate/methanol/diethyl ether solution containing hydrochloric acid to provide 21.9 g of the desired titled compound (m.p. 207°-211° C.).

Workup

  1. customThe titled compound was prepared substantially in accordance with the method
  2. customthat after removing methanol the resultant oil
  3. customwas crystallized from ethyl acetate
  4. customto provide an oily solid
  5. filtrationThis solid was purified by filtration through silica gel using 7% methanol in dichloromethane
  6. customthe resultant residue was recrystallized from an ethyl acetate/methanol/diethyl ether solution
  7. additioncontaining hydrochloric acid

Sources & evidence

ORD record
ord-8b183620c97b4bd8947acc2006b86627
Source dataset
uspto-grants-1995_03
Patent number
US05397798

Reaction notes

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